Synthetic lubricants



. Charles F. Feasley,

United States Patent 2,743,281 SYNTHETIC LUBRICANTS Woodbury, William 'E. Garwood, Haddonfield, Alexander N. Sachanen, Woodbury, and Francis M. Seger, Pitman, N. 1., assignors to Socony Mobil Oil Company, Inc., a corporation of New York No Drawing. Original application August so, 1951, Serial No. 244,482. Divided and this application July 29,1955, Serial No. 527,179

4 Claims. (Cl. 260340.6)

This invention has to dg with the condensation of normal alpha mono-olefins, eterocyclic compounds and organic peroxides, and particularly has to do with the new and useful compositions obtained by said condensation.

This application is a division of our application Serial No. 244,482, filed August 30, 1951, which issued as Patent'No. 2,743,280 on April 24, l95 6.

It is well known in the art to effect a union between molecules of unsaturated hydrocarbons to produce materials called polymers or copolymers, the' molecular weights of which are multiples of the molecular weights of the original hydrocarbons. The operation is called polymerization and the conditions of temperatures, pressure, etc., are called polymerizing conditions.

As is also well known to those familiar with the art,

polymerization reactions'of the type referred to hereinbefore may be conducted at relatively high temperatures and pressures, in the presence of substances ,or of mixtures of substances that promote the polymerization reaction. These substances are referred to as polymerization catalysts.

Several substances have been proposed as polymerizationcatalysts, and among the most widely used are phosphoric acid, sulfuric acid, hydrogen fluoride, aluminum chloride, boron trifluoride and solid alumina-silica absorbents. In polymerization processes involving the use of these substances as catalysts, olefinic hydrocarbons are polymerized into polymeric olefinic hydrocarbons, the molecular weight of which, depending upon the conditions of polymerization, may vary within very broad limits from dimers to polymers containing many thousands of carbon atoms. These products may be used as fuels, lubricants, plastics, etc., depending upon their molecular weights.

It is also well known to those familiar with the art, that ethylene and conjugated diolefinic hydrocarbons, such as butadiene, are readily polymerized in the presence of peroxides or oxygen. This has been embodied in numerous processes which are of considerable commercial importance in the production of high molecular weight plastics and elastomers; In contrast to the polymers formed in the polymerization of ethylene or of conjugated diolefinic hydrocarbons in the presence of acidic polymerization catalysts, the products obtained when peroxides or oxygen are utilized as polymerization catalysts are predominantly high molecular weight polymers.

We have discovered that normal, alpha mono-olefins condense, simultaneously, with certain heterocyclic compounds and with organic peroxides,- under conditions hereinafter defined, with the formation of desirable viscous oils. The oils so formed are characterized by relatively high specific gravity, high viscosity indexand low pour point. Certain of the oils exhibit an unusually high degree of stability to oxidation.

As indicated above, the mono-olefin reactants of this invention are normal or straight chain alpha mono-ole- 2,743,2 Patented Apr. 24, 1S

fins. These olefins contain from about 8 to 18 car] atoms. Such mono-olefins are normally liquid at tl peratures of the order of 20-25 C. Illustrative of s mono-olefins are the following: n-octene-l, n-decent n-dodecene-l, n-hexadecene-l, n-octadecene-l, and like. Preferred, however, of such olefins are those h ing from 8 to 12 carbon atoms, with n-decene-l rep seating 21 particularly desirable olefin. It will be cl from the foregoing examples that an alpha olefin n also be referred to as a l-olefin.

Not only may the mono-olefins of the aforesaid ch actcr be used individually in this invention, but they 1: also be used in admixture with each other. In addith olefin mixtures containing a substantial proportion such mono-olefins may be used. Preferred of such in tures are those containing a major proportion of a l-ole or of l-olefins. Representative of such mixtures are tht obtained by the cracking of parafl'in waxes and other p: afiin products, and those obtained from the FlSCllt Tropsch and related processes.

These hydrocarbon mixtures may contain, in additit to the l-olefin or l-olefins, such materials as: other 0 fins, paraflins, naphthenes and aromatics.

In general, any organic peroxide is suitable for o purpose. By organic peroxide we mean those organ compounds which contain an OO linkage. this connection, it must be clearly understood that wh we speak of organic peroxides herein and in the claims t have reference to organic hydroperoxides as well as simp organic peroxides. The organic peroxides utilizable the process of the present invention may be aliphatic pe oxides, aromatic peroxides, heterocyclie peroxides at alicyclic peroxides. Diethyl peroxide, tertiary butyl h droperoxide, benzoyl peroxide, dimethylthienyl peroxid cyclohexyl peroxide, and lauroyl peroxide may be men tioned by way of non-limiting examples of organic pe; oxides suitable for the process of our invention. in get eral, we prefer to use those organic peroxides containin the radical o nil-0- wherein R is an aliphatic or aromatic radical, such a acetyl peroxide, and of these, we especially prefer to us those containing a benzene ring, such as benzoyl peroxide The organic peroxides may be derived from any suitabl source as is well understood and, advantageously, ma'y b formed in situ, thereby obviating the necessity of usin; the relatively expensive commercial organic peroxides Such a modification must be considered to be within thr scope of the present invention, although the use of in dividual organic peroxides is preferred.

The formation of the organic peroxides in situ may be accomplished in a number of ways. For example, the

may be formed in accordance with the procedure of Price and Krebs (Organic Syntheses, 23, 65 (1943)), or by contacting oxygen or air, preferably moist air, with a suitable organic compound such as a hydrocarbon, or an ether, which reacts therewith to form the desired organic peroxide. Ethyl benzene, cyclo'hexene, and tetralin which readily form peroxides on oxidation, may be mentioned by way of non-limiting examples of organic compounds utilizable for forming the organic peroxides in situ.

In general, and in accordance with our invention, the amounts of organic peroxide to be used are relatively large. In contrast to the polymerization reactions of the prior art which involve conjugated diolefinic hydrocarbons or ethylene wherein organic peroxidesfunction as catalysts in the widely accepted sense of the term, we have found that in our process, the decomposition products of organic peroxides combine with the normal alpha mono-olefins and heterocyclic compounds. Accordingly,

11% yields and nature of the products obtained in the process of the present invention depend upon the amount offiiifd reflect'thdtype of organic p'e roitides employed. For instance, when benzoyl peroxide is reacted with a norm al a m -9 st?! an n arsni tic h d oca b n r n's; wit ca Pipers. produ ts co tainin trut;- i sts i he he es Fr en s re term dl i dsfiionstrtfi by saasnifisatis a ues a t ist s atr d is thi l slz z our PIF$ is one in one Pa nslmsri stion an the ad an more s i i s ta ticsommo ion.

-lfle'ter oc'ycl ic compounds by definition, have a closed chain or ring which contains, in addition to carbon, at least" one -atom of nitrogen, orgyg en sulfur or the like. lqrogyclic cempo nds used herein are those which atfl ti ail l QSlQ Z- il 9r hiq are re is a t Q ti' it; shown by, a simple test procedure. Equal quane's, '10: cc of deceit-Q 1 and of; a, heterocyclic coman hi? m sts in a 25 e g uate and he re u t n "Mi l-W .5 s av s. 9- ?Q ht t w b n web that enias amre s the same a he. sutwimdi ss r t' i i s'r i e i that ded n the mix ur which isa'gi by shaking, the graduate, The maximum temp'era'tui'e deviationdu'ring a ten minpte period. is noted. n, tea s n tem era ure use han. C. sin a Qnpfaivr qwl i n me n assyrat t 0.2 is interpreted as' an indmatipri that the heterocyclic command. i a i y. xid sed. and will be BQP QtiY in the P e t r i 's n. O her was. st sxs'l s c p d showihg a 'te'mpera ture rise of 1 C. or more inthis test trar ifly 9 9. idl w h e. p ide.- h t hu i'litfle r fi t rrsaqt se t, t e hets lqmlisz smnnnnu. nbr'miil alpha mono-olefin and perogridei i it ii Q e. ter s s 129 1 4 ontemh qin n 3 9.w iharsto jrs d x Q idim to'b'e are severaltypical examples given below. In the case of heterpcyelic: compounds containing oxygen or'sulfur, the 'valence requirements of the oxygen and summonses of 2) 'ar,e met by the ring itself. This type'bf heterocyclic is illustrated by dioigane and by thiophen'efeach of-ivhich has a mani rnum temperature deviation of only l- C. The fact that the temp'erature o-the"solution"decreased indicates that energy was required to dissolve the peroxide. Clearly, no oxidation occurred. Other heterocyclics of this type are: furan, pyran, benzofuran, thiapyran, benzothiophenc and mi ut or-H 'Witli nitrogen-containing. heterocyclic compounds, the "1 at a nme ts f he itms n.( al n em 01;,m notbe satisfiedbytherihm Only thosecprnmyr sii gh sh ha a snse aui stnsntsars t a -1h in.s, rq. t astqryr dine. aIp rPi d end q nclineh 'e 'egrangples of operative hetei'oey'clic nitrogen .com-

Ps un s. l insqa 'naximum rim-l isure sv p m the foife'going test 'of 1 C. ln contrast, py-rrole and morpholitie, which have a hydrogen atom attached toa s ss q i rs. emanatin s at sns. i at least 1'0" 'C. and are inoperative herein Nicotine is characterized by one ring nitrogen atom attached to a methyl g on;;; andjkhibits a deviation of +l' l C. It will be apparent, then, that nicotineis unsatisfactoryin the present process. In addition to pyridinealpha-picolinc and quinolin'e, other en enyesnd similarly characterized nit rogen-containing heterocyclic compounds include: isopyrrole; 1,3-isodiazole; pyrimidine andacridine.

Mixedheterocyclic compounds meeting the: aforesaid testrequirement are also considered satisfactory, typical of whichare oxazole, thiazole and benzothiazolef Inoperable mixed heterocyclic compounds include morpholine, phenothiazine and 2-mercaptobenzothiazole.

Heterocyclic compounds; containing relatiyely inert subit g a mime). ls b Sad. aihnrrsssm.p we t. yp o an bs i usat.sr9uns.. t a ides.

representedby chlogine, For eirample, Z-chlorothiophene.

has' ,a,ma:timu m temperature,deviation of.- 1 C. in-the.

a grouping.

foregoing test. In contrast, a mcrcapto group is relatively reactive and should be avoided. By way of illus tration, 3-thiophene thiol has a maximum temperature deviation of +2 C. As indicated above, Z-mercaptobenzothiazole is also unsatisfactory. Alkyl substituents attached to a ring nitrogen atom such as a methyl group attached to a ring nitrogen atom are also to be avoided, as demonstrated by nicotine which contains an N-methyl In accordance with the process of the present invention and depending upon the conditions of operation and the nature of the mono-olefinic hydrocarbon reactants, various condensation products, from comparatively low-boiling to high-boiling fractions, can be synthesized; Thus, in our process, it is possible to produce fractions boiling within the range of those of lubricating oils, i. e., above 700 F. These products are of particular interest and importance. For example, synthetic lubricating oils ob talned in accordance with our process generally have high specific gravities, low pour points and good viscosity characteristics. In contrast to synthetic lubricatingoils obtained in the processes of the prior art involving solely the polymerization of olefiuie hydrocarbons, those of the Present inventionv contain. not only paratfinic chains but also contain heterocyclic nuclei and other structural elements depending upon the organic peroxideand. heterocyclic material used. Further, the synthetic lubricating oils synthesized by the alkylation of aromatics with olefinic hydrocarbons or chlorinated alkanes will. differ materia-lly trom those of our invention due to the very nature of the reactions involved. Thus, as is well. known, the processes involving alkyl'ationreactions utilize strong catalysts which induce a series of side reactions,. such as cracking, isomerization, etc. On the. contrary, in our process, the reaction is effected under conditions whereby side reactions, if any, are. kept to a minimum, and the temperature conditions are comparatively mild. Accord;

ingly, the utilization of our process for the manufacture of synthetic lubricating oils must be considered a preferred, but nevertheless non-limiting embodiment of our invention.

CQNDENSATION CQNDITIQNS.

In carrying out condensation oi theaforesaid roan rants, temperatureswarying;between. about 50 C. and about 200.? C. are usually used,, depending; primarily;v however, upon the kind=of organic peroxideflemployndl Ingeneral,temperaturesof, the-order of Cato 1140. 1 C. are preferredwhen-peroxides areused, reaction-being: substantially. complete, withinabout tenhours at:suc i temperatures.

Whenbenzoyl peroxide is; used;. the temperature may vary between about 50 C. and about 150' C. and, prefer? ably, between about80 C. and C. Onthe other hand, when hydroperoxidesare used, the temperature mayyary between about 100.0,.anal-about-2001 C.,.and: is preferably; 0f.the= order-.of-JTIS G.. The prcssurcotorbe employed depends .uppn ,the. temperature :usedaand; ordi-- narily, a pressuresufiicient to maintain-.therreactantsnin: substantially. a liquid .phase at:the :temperaturecmployed is adequate.

The time.o.reaction-,dcpends upomthe-temperatur...

thenature of the reactants employed, the-quantityof'fre'r actants, and toacertain CXtCl'llrUPOB:thC:PECSSUI'Cr In.

general, the higher-the temperature employed the-shorter: the -reaction, time required-thecriterion .used beingathe time. required .atla given .reactiontemperature to. eflect condensation. and, moreaspecificallwto. assure substantial 1y. complete. consumption of; the-= organic-peroxide: It has, been found that. the..orgg,nie,peroxideis.consumechim the. reactionv by condensation. :with .the olefin-andnhetem cyclic reactants. Thissis.evidenced by; the.peroxide'frag ments present in the oil products. When, therperoxide-Js consumed, no further condensationtakes place and oil products are obtained. Thus-the-time of reaction can be de ig ated. as. one. suflieient toetfeet r condensatiom" Generally, satisfactory results are obtained'when the time period is between about live and about fifteen hours, with the reactants and quantities of reactants such as shown in the illustrative examplesdescribed hereinafter.

'se for oxidation to the peroxide, with the simultaneous or subsequent reaction to bring about the condensation of the mono-olefinic hydrocarbon reactant and the unreacted heterocyclic reactant with that portion of the hetero- As indicated above, the amounts. of organic peroxides 5 cyclic reactant which has been converted to peroxide. and heterocyclic compounds employed determine, to a The process may be carried out as a batch, continuous great degree, the yield and quality of the products. Reor semi-continuous type of operation. Particularly when action may be obtained using between about 0.01 and the process is carried out onacommercial scale, economic about 0.5 molar proportion of a peroxide, with between considerations make it preferable to operate in a conabout 0.01 to about 6.0 molar proportion of a heterocyclic tinuous manner. For eflicient operation, whether the compound, with one molar proportion of a normal, alpha process is carried out on a batch or continuous basis, it is mono-olefin. Preferably, however, we employ organic essential that the mono-olefinic hydrocarbon reactant be peroxides in amounts varying between about 0.05 and intimately contacted with the organic peroxide and with about 0.1 molar proportion, with between about 0.1 and the heterocyclic compound. This may be efiected in about 2.0 molar proportion of heterocyclic compound, several ways and in apparatus which is well known in the with one molar proportion of mono-olefin. In all cases, art. the quantity of peroxide used is a reactive quantity as dis- EXAMPLES anguished from merely a catalytic quantity for the P The following detailed examples are for the purpose oxide reactant enters into the condensation and fragments f illustrating modes f carrying out the process of thereof form components of the eehhehhaheh vprhdhetsinvention. It is to be understood, however, that the in- This is in sharp F h' with Ph h reaehohs of vention is not to be considered as limited to specific rethe P an whleh mvelve whlhgated helehhs ethyl actants or to the specific conditions of operation set forth ene, wherein organic peroxides function as catalysts in herein As will be apparent to those shined in the an, the Widely accepted Sense of the term eathlyhsy a wide variety of other mono-olefinic hydrocarbon re- Ih ehl'l'yihg out the PmeeSS of the Present lhvehhoh the actants, heterocyclic reactants, and organic peroxides may organic peroxide is added to the mono-olefin and hetero he used cyclic compound, preferably in two or more portions'at The geharal Procedure foll d in the making f the intervals of a few hehrs- If desired: the Orgahie e j example runs was substantially the same in all cases. The ide may he added in some instances ih a single h olefin reactant and the heterocyclic reactant were stirred although excessive heat of reaction may be developed. together and heated while the peroxide was added at When the organic peroxide is formed in situ, a mixture tel-V2118. A temperature f 80 to and a time f ef the mohoolehh heterocyclic eempouhd and an about nine to ten hours were found suflicient to cause the organic eempohhd which forms an Organic Perexide n reaction to go to substantial completion. The crude resubjected to oxidation, in amounts of at least about 5%, action pwduct was f ed f low molecular weight Preferably at least about based on the Weight ponents and the desirable condensation products were obthe monoolcfinic hydrocarbon reactant, is contacted with mined as oily residues s f the peroxide fragments Oxygen for p under the eohditiohs of were eliminated as benzoic acid and then removed by action to produce the organic peroxide n Sitll at the alkali washing or by distillation. This can be considered same time that the eehdehseheh reaction cure The to be an operating loss. The unreacted olefins, recovered Contact with Oxygen y be efieeted y hgimmh of by distillation, were suitable for recycling. The oily prodmhmh'e in hhhbhhg of the air through the mixture uct was tested without any other treatment, refining and without additives.

In another embodiment of this medlfieehoh, an ergame To distinguish the condensation products from the discompound is peroxidized to a desired degree before the tillate fractions thereof, the oily residues are identified addition of the Olefihie hydl'eeal'hoh reactant and the as residual oils. The latter term identifies the oils from heterocyclic reactant. Yet another modification is to use which uhreacmd materials, byproducts (as any henzoic the moheolefihie hydfeeal'heh reaetaht P Se for oxide acid) and products of intermediate boiling range have tion to the peroxide, with simultaneous or subsequent rebeen separated action to bring about the eohdehsafieh 0f the hhreaeted All of the tests and analyses to which the residual oils mello-olefihie hydrocarbon reactant e the heterocyclic in Table I were subjected are well known standard tests. reactant, with that Portion of the mohe-olefinic y In this connection, it will be noted that the designation carbon which has been converted to peroxide. Still an- N. N. refers to the neutralization number, which is a other modification is to use the heterocyclic reactant per measure of the acidity of the oil.

' Table 1 Run No 1 2 a 4 5 6 fi iffiyw'anriij hi 225 323 hiifflii: iziifffiflii 223 Molar Proportlom. 1 '4 '4 0.5.. 3 3. Heterocycllmn. Thlophene- Dloxane..... Pyrldine. AlIpnha-Pieo- Nleotlne.... Morphollne.

Parts by Weight s4 264 237 279 162.. 268.

Molar Proportlon 1 3 '4 3... 1 3. Pero de Benzoyl Benzoyl..--. Benzoyl.. Benzoyl.. Benzoy1..-.- Benzoyl.

Parts by Weight.. 24 72 72 12 72. sm ari 2:- a" Tlme rs s w y Residual on;

Paris by Weight.. 128

Percen Yield 20. 17.5.--

sit-sass as fi iii ii i 24.2.- 13.1-. 15.5-.-

s c Gravlty..' o.s705.--.--- 3129-- mu en l i dii 0.73.. 1.63.. 7.52.

Footnote: at end of table.

Table l-Continued Run'No Mono-olefin Parts by Weight. Molar Propor m1 Hotarocycllc lerts by Weigh 280 a Mercapto-benzothlazole.

' niDecene-l a Thtophenethlol.

ai flendecane- ,1,

tlhlophene.

35 Molar Proportion 1 Peroxide Parts by'Welght 72 Molar Propor V. Pour Point,

Br. Addn. N Spec inc Gravity Sapoiifllcation'No Sullnr, Pornnnf NltrogemPeroent 1 Pcroenthydrogen, 12.67; percent uarbon, 8l.88. 1 Molecular weight- 407.

= Thlophene tended to boil out and periodic ro-addltton or this material was made.

In Table I above, runs 1-4 illustrate excellent synthetic oils obtained with the present invention. All ofthcoils of runs 1-4 have high viscosity indices (91- 112) and have desirably low .pour points. Run 1 is illustrative of an oil obtained with a suitable sulfur-containing'heterd cyclic compound, thiophene, and run 2 is illustrative of an oil obtained with a suitable oxygen-contaiuing heterocyclic compound, dioxane. Pyridine and alphapicoline in runs 3 and 4, respectively, illustrate operative nitrogen-containing heterocyclic compounds. The low yield obtained in run 4 with alpha-picoline is due to a high ratio of the heterocyclic compound to olefin; with lower ratios, increasing yields of desirable oils may be obtained.

Run 5 is illustrative of the low degree of reaction or condensation obtained with nicotine, which is too readily oxidized to be used herein.

Run 6, in which morpholine is used, .is also illustrative of too readily oxidizable nitrogen-containing heterocyclic compounds. The morpholine product was made from a reaction mixture containing a. relatively small amount of morpholine. Low viscosity index and high nitrogen content indicate little reaction of the olefin and much side reaction of morpholine with peroxide.

Mercaptobcnzothiazole, in run 7, is another unsatisfactory heterocyclic compound, as shown by the very low viscosity index, 2.6, of the oil product. The high sulfur content of the oil product is indicative of relatively little reaction of olefin, heterocyclic compound and peroxide.

Run 8 shows a mixed heterocyclic compound, phenothiazine, which is too readily oxidized to be of value in this invention. Similarly, run 9 shows a substituted heterocyclic having a highly reactive substituen't group, mercapto or thiol.

Runs 10 and 11 are illustrative of oils obtained from a relatively long chain olefin, n hexadecene-i. It will be noted that'these oils have desirably high viscosity indices, 124.5 and 137.3, respectively.

As will be evident from the data presented above in Table I, the condensation products of this invention are highly desirable lubricants per se. They are also of considerable value as blending agents for other lubricating oils. They impart desirable viscosity index (V. I.) and pour point characteristics to the oils in combination therewith, for, as indicated above, they have advantageous viscosity and pour point properties. In short, the synthetic oils find utility in upgrading other lubricants. Typical oils with which the synthetic oils may lac-blended are mineral oils such as are normally used in internal combustion and turbine engines. When so blended, the

' syntheticoilsmay comprise themajor proportion of the thetic lubricants ofthis :invention .may be further improved by incorporating therewith a small but eliective amount, of anaddition-agent-such as an antioxidant, a detergent-an extreme pressure agent, afoam suppressor, a viscosity index I.) improver, etc. Antioxidants for iviscous oilsarewell known in the art, and generally contain sulfur, nitrogen, oxygen and/or phosphorus. Representative ofsuoh antioxidants is a phosphorus-andsulfur containing reaction product of pinene and P255. Typical detergents which .may be so used are metal salts of .alkyl-sub'stituted aromatic sulfonic or carboxylic acids, as illustrated by diwax benzene barium sulfonate and barium phenate, barium salt of a wax-substituted phenol carboxylicacid. Extreme pressure agents are well known; illustrating such materials are numerous chlorine and/or sulfur containing compositions, one such material being a chlorenaphtha .xanthate. Silicones, such as dimethyl silicone, may be used to illustrate foam suppressing compositions. Viscosity index improving agents which may be .used are typified 'by polypropylenes, polyisobutyilenes, polyacrylatc esters, and the like.

contemplated also as within the scope of this invention is a method oflubricating relativelynioving surfaces by maintainingtherebetween a film consisting of any of theaforesaid oils.

It is to be understood that the foregoing description and representative examples are non-limiting and serve to illustrate the invention, which is to be broadly construed in 'the llight of the language of the appended claims.

1. An oil of lubricating viscosity characterized by relatively high specific gravity, high viscosity index and low pour ,point and obtained by: -condensing, at a temperature of about C. for about nine hours, one molar proportion of n-decene-l with one molar proportion of dioxane and -0.1 molar proportion of benzoyl peroxide, and separating said oil from the reaction product thus formed. 1

2. The process tor-preparing an oil of lubricating viscosity characterized by relatively high specific gravity, high viscosity index and low pour point which comprises: heating, at atemperatui'e of about 85 C. for about nine hours,=one molar proportion-of n-decene-l with one molar proportion of dioxane and 0.1 molar proportion of benzoyl peroxide, and separating said oil from the reaction product thus formed.

3. An oil of lubricating viscosity characterized by relatively high specific gravity, high viscosity index and low pour point and obtained by: heating at a temperature "of between about 80 C. and about 140 (3. for a period of time between about five hours and about ten hours, one molar proportion of a normal alpha-mono olefin having from about 8 to 18 carbon atoms per molecule, between about 0.01 and about 0.5 molar proportions of an organic peroxide selected from the group consisting of tertiary butyl peroxide and benzoyl peroxide, and from about one to six molar proportions of dioxane, and separating said oil from the reaction product thus formed.

4. The process forpreparing an oil of lubricating viscosity characterized by relatively high specific gravity, high viscosity index and low pour point which comprises: heating at a temperature of between about 80 C. and about 140 C. for a. period of time between about five hours and about ten hours, one molar proportion of a normal alpha-mono olefin having from about 8 to 18 carbon atoms per molecule, between about 0.01 and about 0.5 molar proportions of an organic peroxide selected from the group consisting of tertiary butyl peroxide and benzoyl peroxide, and from about one to six molarproportions of dioxane, and separating said oil from the re action product thus formed. a

No references cited. 

1. AN OIL LUBRICATING VISCOSITY CHARACTERIZED BY RELATIVELY HIGH SPECIFIC GRAVITY, HIGH VISCOSITY INDEX AND LOW POUR POINT AND OBTAINED BY: CONDENSING, AT A TEMPERATURE OF ABOUT 85* C. FOR ABOUT NINE HOURS, ONE MOLAR PROPORTION OF N-DECENE-1 WITH ONE MOLAR PROPORTION OF DIOXANE AND 0.1 MOLAR PROPORTION OF BENZOYL PEROXIDE, AND SEPARATING SAID OIL FROM THE REACTION PRODUCT THUS FORMED. 